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Issue 10, 2010
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Visible light flavin photo-oxidation of methylbenzenes, styrenes and phenylacetic acids

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Abstract

We report the photocatalytic oxidation of benzylic carbon atoms under mild conditions using riboflavin tetraacetate as photocatalyst and blue-emitting LEDs (440 nm) as light source. Oxygen is the terminal oxidant and hydrogen peroxide appears as the only byproduct in most cases. The process oxidizes toluene derivatives, stilbenes, styrenes and phenylacetic acids to their corresponding benzaldehydes. A benzyl methyl ether and acylated benzyl amines are oxidized directly to the corresponding methyl ester or benzylimides. The mechanism of the reactions has been investigated and the results indicate that oxygen addition to benzyl radicals is a key step of the oxidation process in the case of phenylacetic acids.

Graphical abstract: Visible light flavin photo-oxidation of methylbenzenes, styrenes and phenylacetic acids

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Publication details

The article was received on 29 Jun 2010, accepted on 05 Aug 2010 and first published on 14 Sep 2010


Article type: Paper
DOI: 10.1039/C0PP00202J
Citation: Photochem. Photobiol. Sci., 2010,9, 1367-1377
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    Visible light flavin photo-oxidation of methylbenzenes, styrenes and phenylacetic acids

    R. Lechner, S. Kümmel and B. König, Photochem. Photobiol. Sci., 2010, 9, 1367
    DOI: 10.1039/C0PP00202J

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